Synthetic resin and process of producing it



Patented Apr. 30, 1935 I a 1,999,380

UNITED 'STATES PATENT OFFICE SYNTHETIC RESIN AND PROCESS OF PRODUCING ITi John Morris Weiss, New York, N. Y., assignor to Weiss and Downs, Inc.,New York, N. Y., a corporation oi New York No Drawing. ApplicationNovember 17, 1933,

Serial No. 698,501

9 Claims. (Cl. 260-2) This invention relates to a'type of syntheticdextrose (corn sugar) added gradually, stirring resin and the process ofproducing it. The procand, maintaining the temperature at 150 C. esscomprises treating a mcnosaccharide such as After all the dextrose isadded, the temperature dextrose with a dibasic organic acid or. an anisgradually raised over about one hour to 170 5 hydride 01' a dibasic acidsuch as phthalic an- C. During the process, water vapor is evolved 6hydride or maleic acid anhydrlde. The characand the mass thickens andbecomes someter of the products varies, dependent on the what darker incolor. It'is poured out into a particular raw materials selected and themanmold and allowed to solidify, forming a hard net in which thecondensation is carried on. brittle resin with a specific gravity ofabout 1.49 10 Example I.-0ne hundred parts by weight of at 25 C. l0maleic acid anhydride are melted and heated The product is practicallyinsoluble in cold with agitation at 110 G. Then one hundred water,partly soluble in boiling water and is and eighty parts by weight ofcorn sugar (dexbroken up on continued boiling to a part solutrose) aregradually added with contlnuing-agitlon and a part suspension. It isreadily soli-5 tation. Some cooling takes place from the aduble inmethanol, ethyl alcohol, isopropyl aldition of the corn sugar and whenthe temperacohol, and dioxan, and insoluble or only slightly 7 turereaches 110 0. again a homogeneous liqsoluble in benzol, carbontetrachloride and -uid mass results. The temperature is graduallyethylene dichloride. If the methanol solution raised and the massirothsand gives oil water is diluted with water, a very fine precipitate isvapor. The mixture darkens somewhat and obtained. thickens as theheating progresses. 'Aiter the A portion of the product baked at 165 C.for temperature reaches 150" 0., the product is 1% hours more, darkenedslightly incolor but drawn off and allowed to cool. its solubilityin thevarious solvents is the same The brow'nsolid obtained is a hard cake ofa as in the case of the unbaked product except specific gravity of about1.480 at 25 C. which that its solubility in hot water is decreased. 25

can readily be reduced to a powder. It is read On evaporating themethanol solution of this ily soluble in water but relatively insolublein heat treated product, clear transparent films of cold 95% ethylalcohol. 'Othersolubilities noted the resin are obtained.

are l Example III.--A mixture of 50 parts by weight o1 maleic acidanhydride and '75 parts 01' phthallc 30 gggj 'g if jjj mfg? mmluble'anhydride are heated and stirred. At 100 0. Ethylene dichloride 1:.insoluble when the maleic anhydiide is melted and the m alcohol solublephthallc anhydnde only partly melted, 180 parts nicmorethyl ethe;insoluble of dextrose are added. The mass then works up DioxmL insolublelike a dough and gradually melts as the tempera- 35 ture is raised to150 C. The mixture is com- When the product is treated with methanol,'pletely homogeneous and after stirring for 20 it appears slightlysoluble in the cold and partly minutes at 150 C. is poured out andallowed to soluble and partly dispersed on boiling. The solidify. 40boiled solution after filtering is clear but after This product has aspecific gravity at 25 C. of 40 c o in nd an n s o a urther separationabout 1.36 and is readily. soluble in water, in- OI SOIidS- Even af rprol n ed s anding at room soluble in benzol, carbon tetrachloride andtemperature, a substantial portion of the prodethylene dichloride, andonly partly soluble in not remains in solution. ethyl alcohol anddioxan. With methanol it goes On taking the resin i'ormed as abovedescribed into solution with difliculty after considerable 45 andheating at 150 C. for four hours, it shows a heating with a slightamount of insoluble residue. loss in weight of less than 5% and afterthe heat- A portion of the product was baked at ing, is insoluble inboth water and cold methanol. 120-135 C. for five hours. The loss inweight In 1101; methanol and with P ed heating. a was negligible but theproduct became rather partial solution is noted. The heated product isporous and lost its resinoid appearance. It an- 50 Somewhat rub e y w hon hard nd o gh peared opaque due apparently to the inclusion when cold.of numerous minute bubbles. Its solubllities Example II.One hundred andfifty parts by were the same as with the unbakedproduct exweig'ht ofphthallc acid anhydride are heated cept that it was now readily solublein methanol to c. and one hundred and eighty parts or without continuedboiling. 55

' used and the claims Example IV.-One hundred and eighteen parts byweight of succinic acid and one hundred and eighty parts of cerulose aremixed and gradually heated to 175 C. forming a homogeneous mass. Thetemperature is maintained around 175 C. for a short timev and thenremoved from the reaction vessels and allowed to cool and solidify. Adark, hard resinous material results. The product is readily soluble inwater and methanol, slowly soluble in ethyl alcohol and insoluble inbenzol, carbon tetrachloride. dioxan and ethylene dichloride. It isbrittle and is readily powdered.

The process has been described specifically in connection with dextrosebut other hexoses (a sugarcontaining 6 carbon atoms) such as 1aev ulose, mannose, galactose and various aldo and keto hexoses'may beemployed as one raw material. Similarly other anhydrides of dibasicacids can be employed as the other raw material for the synthesis of theresin. In some cases the acid itself rather than the anhydride can be'used as, for example, maleic acid or acetylene dicarboxylic acid. Ingeneral the acid and anhydride belong to the class which have at leasttwo carboxyl groups attached to adjacent carbon atoms. Anhydrides whichhave been found quite suitable have the carboxyl groups attached toadjacent carbon atoms which atoms are joined by a double or triplelinkage. Thus, both maleic and phthalic anhydride contain the groupMixed anhydrides, or mixedhexoses, may be are intended to cover mixturesunder the term hexose" or "anhydride".

The time and temperature of the mixing operation can be varied overrather wide limits. it however being necessary to keep the temperaturebelow the point at which undesirable carbonization takes place.

- The resins have thermoplastic properties and may be used as binders inthe water soluble state and afterward the product may be renderedinsoluble in water by suitable heat treatment. The alcohol solublevarieties may be .used as lacquer constituents and the alcohol solutionsform a convenient way or using the resins as impregnating compounds.

which comprises mixing Having thus described my invention, 1 claim:

1. The process of producing a water soluble resinous product whichcomprises-mixing and heating a hexose with an anhydride'oi adicarboxylic organic acid at a temperature not exceeding C.

2. The process of producing a water soluble resinous product whichcomprises mixing and heating a hexose with an organic acid 'anhrdridecontaining the group ,at a temperature not exceeding 1'10 C.

3. The process oi producing a water soluble resinous product whichcomprises mixing and heating dextrose and maleic acid anhydride at atemperature not exceeding 1'10? 0.

4. As a new article t manufacture, a water. soluble resinous productmade by mixing and heating dextrose with maleic acid anhydride at atemperature not exceeding 170 C.

p 5. As a new article of manuiactm'e, a we soluble resinous product madeby mixing and heating dextrose with phthalic acid anhydride at atemperature not exceeding 1'10 0.

6. The process of producing a resinous product which comprises mixingand heating a hoxose with an anhydride of a dicarboxylic organic acid ata temperature belowi'l5' C.

7. The process of producing a resinous product and heating dextrose withan organic acid anbydride the 11-00 L. \o oo at a temperature below C.

8. The process of producing a resinous product which comprises mixingand heating dextrose with phthalic anhydride at a temperature below1'15- c. v

9. The process of producing a resinous product which comprises mixingand heating dextrose with maleic acid anhydride at low 175 C. I

- JOHN MORRIS WEISS.

atemperature bo- 5

